Provided is an information processing apparatus that effectively utilizes contexts and has the highly convenient messaging function, a method thereof and a terminal device used for message communication. The information processing apparatus includes a communication section and a control section. The communication section communicates a message between respective terminal devices used by a plurality of users. The control section acquires is a context of one or more users among the plurality of users, and controls at least one of creation or communication of message-related information including content or a format of the message on the basis of the acquired context.